catena-Poly[[(1,10-phenanthroline-κ(2) N,N')copper(II)]-μ-2,2'-iminodibenzoato-κ(4) O,O':O'',O'''].

The structure of the title compound, [Cu(C14H9NO4)(C12H8N2)] n , consists of zigzag polymeric chains along the c axis. The asymmetric unit contains one Cu(II) atom which is coordinated by one 2,2'-imino-dibenzoate ligand and a one phenanthroline unit. Two intra-molecular N-H⋯O hydrogen bonds occur. The supra-molecular structure is characterized by weak C-H⋯O hydrogen bonds and π-π stacking inter-actions, forming a three-dimensional supramolecular network. The shortest centroid-centroid distances between neighbouring phenanthroline aromatic rings and 2,2'-imino-dibenzoate rings are 3.684 (1) and 3.640 Å, respectively. The shortest intra-chain Cu⋯Cu distance is 7.2885 (9) and the shortest Cu⋯Cu distance between Cu atoms in different chains is 7.1103 (6) Å.

Related literature

For general background to CuII low-dimensional polynuclear magnetic materials, see: Fabelo et al. (2009 ▶); Martins et al. (2008a ▶,b ▶); Silva et al. (2001 ▶); Yuste et al. (2007 ▶, 2008 ▶). For structural and coordination information for 2,2′-iminodi­benzoic acid, see: Field & Venkataraman (2002 ▶); Gao et al. (2009 ▶); Lin et al. (2006 ▶).

Experimental

Crystal data

[Cu(C14H9NO4)(C12H8N2)]

M = 498.98

Monoclinic,

a = 31.7536 (6) Å

b = 9.8492 (2) Å

c = 14.4865 (3) Å

β = 113.222 (1)°

V = 4163.56 (14) Å3

Z = 8

Mo Kα radiation

μ = 1.09 mm−1

T = 293 K

0.1 × 0.08 × 0.07 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.898, T max = 0.971

36778 measured reflections

3976 independent reflections

2900 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.089

S = 1.02

3976 reflections

307 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.40 e Å−3

Data collection: APEX2 (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813009203/bt6890sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813009203/bt6890Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cu(C14H9NO4)(C12H8N2)]	F(000) = 2040
Mr = 498.98	Dx = 1.592 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6606 reflections
a = 31.7536 (6) Å	θ = 2.2–20.8°
b = 9.8492 (2) Å	µ = 1.09 mm−1
c = 14.4865 (3) Å	T = 293 K
β = 113.222 (1)°	Blocks, green
V = 4163.56 (14) Å3	0.1 × 0.08 × 0.07 mm
Z = 8

Bruker APEXII CCD area-detector diffractometer	3976 independent reflections
Radiation source: fine-focus sealed tube	2900 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.061
φ and ω scans	θmax = 25.8°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −38→38
Tmin = 0.898, Tmax = 0.971	k = −12→12
36778 measured reflections	l = −17→17

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.037P)2 + 5.032P] where P = (Fo2 + 2Fc2)/3
3976 reflections	(Δ/σ)max < 0.001
307 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Cu1	0.172485 (11)	0.45882 (4)	0.30778 (3)	0.03710 (12)
N1	0.07823 (8)	0.7287 (3)	0.46195 (18)	0.0466 (6)
H1	0.1021	0.6781	0.4882	0.056*
N2	0.20508 (7)	0.2788 (2)	0.35164 (16)	0.0361 (5)
N3	0.23714 (7)	0.5223 (2)	0.34707 (17)	0.0370 (5)
O4	0.11136 (6)	0.6223 (2)	0.75794 (15)	0.0448 (5)
O1	0.14757 (7)	0.6413 (2)	0.27927 (16)	0.0479 (5)
O2	0.14659 (7)	0.6025 (2)	0.42821 (15)	0.0495 (5)
O3	0.13160 (6)	0.5939 (2)	0.63028 (15)	0.0441 (5)
C1	0.13485 (9)	0.6710 (3)	0.3501 (2)	0.0387 (7)
C2	0.10555 (8)	0.7946 (3)	0.3344 (2)	0.0361 (7)
C3	0.10490 (9)	0.8884 (3)	0.2622 (2)	0.0444 (7)
H3	0.1217	0.8703	0.2237	0.053*
C4	0.08029 (11)	1.0071 (3)	0.2458 (3)	0.0539 (9)
H4	0.0798	1.0670	0.1957	0.065*
C5	0.05662 (10)	1.0354 (3)	0.3043 (3)	0.0560 (9)
H5	0.0414	1.1179	0.2967	0.067*
C6	0.05500 (10)	0.9437 (3)	0.3744 (3)	0.0528 (8)
H6	0.0379	0.9641	0.4120	0.063*
C7	0.07871 (9)	0.8197 (3)	0.3902 (2)	0.0384 (7)
C8	0.04358 (9)	0.7090 (3)	0.4972 (2)	0.0414 (7)
C9	−0.00235 (10)	0.7313 (4)	0.4351 (3)	0.0537 (9)
H9	−0.0099	0.7659	0.3708	0.064*
C10	−0.03645 (10)	0.7024 (4)	0.4680 (3)	0.0603 (10)
H10	−0.0669	0.7152	0.4249	0.072*
C11	−0.02635 (10)	0.6550 (4)	0.5636 (3)	0.0605 (10)
H11	−0.0497	0.6372	0.5855	0.073*
C12	0.01899 (10)	0.6343 (3)	0.6269 (3)	0.0492 (8)
H12	0.0262	0.6032	0.6919	0.059*
C13	0.05402 (9)	0.6595 (3)	0.5942 (2)	0.0383 (7)
C14	0.10206 (9)	0.6238 (3)	0.6641 (2)	0.0381 (7)
C15	0.18760 (10)	0.1574 (3)	0.3531 (2)	0.0440 (7)
H15	0.1561	0.1494	0.3341	0.053*
C16	0.21466 (11)	0.0407 (3)	0.3820 (2)	0.0502 (8)
H16	0.2012	−0.0432	0.3822	0.060*
C17	0.26097 (11)	0.0504 (3)	0.4102 (2)	0.0500 (8)
H17	0.2793	−0.0266	0.4299	0.060*
C18	0.28067 (10)	0.1772 (3)	0.4090 (2)	0.0421 (7)
C19	0.32883 (10)	0.2002 (4)	0.4383 (2)	0.0519 (8)
H19	0.3491	0.1273	0.4580	0.062*
C20	0.34496 (10)	0.3263 (4)	0.4376 (2)	0.0515 (8)
H20	0.3764	0.3388	0.4582	0.062*
C21	0.31555 (9)	0.4409 (3)	0.4063 (2)	0.0409 (7)
C22	0.32977 (11)	0.5755 (4)	0.4042 (2)	0.0516 (9)
H22	0.3607	0.5948	0.4229	0.062*
C23	0.29850 (11)	0.6773 (3)	0.3750 (2)	0.0523 (8)
H23	0.3080	0.7664	0.3737	0.063*
C24	0.25214 (10)	0.6482 (3)	0.3469 (2)	0.0454 (7)
H24	0.2311	0.7190	0.3274	0.055*
C25	0.26837 (9)	0.4207 (3)	0.3767 (2)	0.0357 (6)
C26	0.25100 (9)	0.2879 (3)	0.3789 (2)	0.0351 (6)

	U11	U22	U33	U12	U13	U23
Cu1	0.03325 (18)	0.0380 (2)	0.0386 (2)	0.00164 (16)	0.01251 (14)	−0.00015 (17)
N1	0.0341 (13)	0.0582 (17)	0.0465 (16)	0.0182 (12)	0.0148 (11)	0.0099 (13)
N2	0.0334 (12)	0.0379 (14)	0.0331 (13)	−0.0015 (10)	0.0091 (10)	−0.0031 (11)
N3	0.0373 (12)	0.0364 (14)	0.0364 (13)	−0.0009 (11)	0.0137 (10)	−0.0022 (11)
O4	0.0373 (10)	0.0534 (13)	0.0395 (12)	0.0011 (10)	0.0106 (9)	−0.0050 (10)
O1	0.0541 (12)	0.0437 (12)	0.0529 (13)	0.0095 (10)	0.0286 (11)	0.0050 (11)
O2	0.0522 (12)	0.0514 (13)	0.0428 (13)	0.0222 (10)	0.0166 (10)	0.0085 (11)
O3	0.0325 (10)	0.0517 (13)	0.0484 (13)	0.0064 (9)	0.0162 (9)	0.0097 (10)
C1	0.0311 (14)	0.0354 (16)	0.0434 (18)	0.0016 (12)	0.0081 (13)	−0.0023 (14)
C2	0.0276 (13)	0.0328 (16)	0.0384 (16)	0.0010 (11)	0.0029 (12)	−0.0023 (13)
C3	0.0379 (15)	0.0434 (18)	0.0443 (18)	−0.0045 (14)	0.0081 (13)	−0.0003 (15)
C4	0.0439 (17)	0.0402 (18)	0.063 (2)	−0.0025 (14)	0.0055 (16)	0.0098 (16)
C5	0.0418 (17)	0.0348 (18)	0.071 (2)	0.0068 (15)	−0.0001 (16)	0.0034 (18)
C6	0.0398 (16)	0.051 (2)	0.059 (2)	0.0143 (15)	0.0105 (15)	−0.0053 (17)
C7	0.0285 (14)	0.0407 (17)	0.0370 (17)	0.0064 (12)	0.0033 (12)	0.0004 (14)
C8	0.0330 (15)	0.0418 (17)	0.0445 (18)	0.0066 (13)	0.0101 (13)	−0.0051 (14)
C9	0.0355 (16)	0.067 (2)	0.052 (2)	0.0124 (15)	0.0096 (14)	−0.0008 (17)
C10	0.0299 (16)	0.072 (3)	0.069 (3)	0.0086 (16)	0.0089 (16)	−0.005 (2)
C11	0.0356 (17)	0.068 (2)	0.083 (3)	−0.0017 (16)	0.0282 (17)	−0.006 (2)
C12	0.0401 (16)	0.052 (2)	0.056 (2)	−0.0007 (15)	0.0197 (15)	−0.0052 (16)
C13	0.0289 (14)	0.0340 (16)	0.0484 (18)	0.0012 (12)	0.0113 (12)	−0.0069 (14)
C14	0.0334 (15)	0.0320 (16)	0.0460 (19)	−0.0047 (12)	0.0125 (13)	−0.0006 (14)
C15	0.0420 (16)	0.0425 (19)	0.0415 (18)	−0.0063 (14)	0.0100 (13)	−0.0033 (14)
C16	0.064 (2)	0.0330 (17)	0.0458 (18)	−0.0072 (16)	0.0138 (15)	−0.0010 (15)
C17	0.060 (2)	0.0400 (18)	0.0423 (18)	0.0115 (16)	0.0119 (15)	−0.0002 (15)
C18	0.0449 (16)	0.0439 (18)	0.0341 (17)	0.0076 (14)	0.0120 (13)	−0.0006 (14)
C19	0.0391 (17)	0.064 (2)	0.050 (2)	0.0151 (16)	0.0141 (14)	0.0007 (17)
C20	0.0322 (15)	0.073 (2)	0.050 (2)	0.0047 (16)	0.0167 (14)	−0.0047 (18)
C21	0.0343 (14)	0.056 (2)	0.0358 (16)	−0.0040 (14)	0.0170 (12)	−0.0041 (15)
C22	0.0399 (17)	0.070 (2)	0.048 (2)	−0.0164 (16)	0.0203 (14)	−0.0093 (17)
C23	0.060 (2)	0.050 (2)	0.051 (2)	−0.0174 (17)	0.0258 (16)	−0.0057 (16)
C24	0.0505 (18)	0.0392 (18)	0.0472 (19)	−0.0048 (14)	0.0200 (15)	−0.0043 (15)
C25	0.0356 (14)	0.0425 (17)	0.0295 (15)	−0.0012 (12)	0.0135 (12)	−0.0031 (12)
C26	0.0361 (14)	0.0399 (16)	0.0284 (15)	0.0021 (12)	0.0117 (12)	−0.0006 (13)

Cu1—O1	1.942 (2)	C8—C13	1.397 (4)
Cu1—O4i	1.9548 (19)	C9—C10	1.375 (4)
Cu1—N3	2.002 (2)	C9—H9	0.9300
Cu1—N2	2.025 (2)	C10—C11	1.374 (5)
Cu1—O3i	2.4360 (19)	C10—H10	0.9300
Cu1—C14i	2.515 (3)	C11—C12	1.383 (4)
N1—C7	1.377 (4)	C11—H11	0.9300
N1—C8	1.398 (4)	C12—C13	1.392 (4)
N1—H1	0.8600	C12—H12	0.9300
N2—C15	1.322 (4)	C13—C14	1.503 (4)
N2—C26	1.355 (3)	C14—Cu1ii	2.515 (3)
N3—C24	1.329 (4)	C15—C16	1.397 (4)
N3—C25	1.354 (3)	C15—H15	0.9300
O4—C14	1.272 (3)	C16—C17	1.366 (4)
O4—Cu1ii	1.9548 (19)	C16—H16	0.9300
O1—C1	1.276 (3)	C17—C18	1.399 (4)
O2—C1	1.241 (3)	C17—H17	0.9300
O3—C14	1.253 (3)	C18—C26	1.393 (4)
O3—Cu1ii	2.4360 (19)	C18—C19	1.435 (4)
C1—C2	1.494 (4)	C19—C20	1.345 (5)
C2—C3	1.389 (4)	C19—H19	0.9300
C2—C7	1.409 (4)	C20—C21	1.421 (4)
C3—C4	1.373 (4)	C20—H20	0.9300
C3—H3	0.9300	C21—C25	1.400 (4)
C4—C5	1.366 (5)	C21—C22	1.404 (4)
C4—H4	0.9300	C22—C23	1.357 (4)
C5—C6	1.374 (5)	C22—H22	0.9300
C5—H5	0.9300	C23—C24	1.394 (4)
C6—C7	1.406 (4)	C23—H23	0.9300
C6—H6	0.9300	C24—H24	0.9300
C8—C9	1.397 (4)	C25—C26	1.425 (4)
O1—Cu1—O4i	92.16 (9)	C11—C10—C9	121.2 (3)
O1—Cu1—N3	93.31 (9)	C11—C10—H10	119.4
O4i—Cu1—N3	171.94 (9)	C9—C10—H10	119.4
O1—Cu1—N2	172.92 (9)	C10—C11—C12	119.1 (3)
O4i—Cu1—N2	93.93 (9)	C10—C11—H11	120.5
N3—Cu1—N2	81.03 (9)	C12—C11—H11	120.5
O1—Cu1—O3i	88.28 (8)	C11—C12—C13	120.7 (3)
O4i—Cu1—O3i	58.99 (7)	C11—C12—H12	119.6
N3—Cu1—O3i	115.25 (8)	C13—C12—H12	119.6
N2—Cu1—O3i	97.95 (8)	C12—C13—C8	120.0 (3)
O1—Cu1—C14i	88.22 (9)	C12—C13—C14	117.6 (3)
O4i—Cu1—C14i	29.85 (8)	C8—C13—C14	122.3 (2)
N3—Cu1—C14i	144.48 (9)	O3—C14—O4	121.4 (2)
N2—Cu1—C14i	98.86 (9)	O3—C14—C13	120.6 (3)
O3i—Cu1—C14i	29.27 (8)	O4—C14—C13	118.0 (2)
C7—N1—C8	127.7 (2)	O3—C14—Cu1ii	71.87 (15)
C7—N1—H1	116.1	O4—C14—Cu1ii	49.89 (13)
C8—N1—H1	116.1	C13—C14—Cu1ii	165.6 (2)
C15—N2—C26	117.7 (2)	N2—C15—C16	122.5 (3)
C15—N2—Cu1	129.13 (19)	N2—C15—H15	118.8
C26—N2—Cu1	113.09 (18)	C16—C15—H15	118.8
C24—N3—C25	118.2 (2)	C17—C16—C15	119.6 (3)
C24—N3—Cu1	128.2 (2)	C17—C16—H16	120.2
C25—N3—Cu1	113.59 (18)	C15—C16—H16	120.2
C14—O4—Cu1ii	100.26 (16)	C16—C17—C18	119.5 (3)
C1—O1—Cu1	105.80 (18)	C16—C17—H17	120.2
C14—O3—Cu1ii	78.86 (16)	C18—C17—H17	120.2
O2—C1—O1	122.2 (3)	C26—C18—C17	116.8 (3)
O2—C1—C2	121.8 (3)	C26—C18—C19	118.6 (3)
O1—C1—C2	116.0 (3)	C17—C18—C19	124.5 (3)
C3—C2—C7	118.8 (3)	C20—C19—C18	120.5 (3)
C3—C2—C1	118.7 (3)	C20—C19—H19	119.7
C7—C2—C1	122.4 (3)	C18—C19—H19	119.7
C4—C3—C2	122.4 (3)	C19—C20—C21	122.1 (3)
C4—C3—H3	118.8	C19—C20—H20	118.9
C2—C3—H3	118.8	C21—C20—H20	118.9
C5—C4—C3	118.7 (3)	C25—C21—C22	116.2 (3)
C5—C4—H4	120.6	C25—C21—C20	118.3 (3)
C3—C4—H4	120.6	C22—C21—C20	125.5 (3)
C4—C5—C6	121.0 (3)	C23—C22—C21	120.2 (3)
C4—C5—H5	119.5	C23—C22—H22	119.9
C6—C5—H5	119.5	C21—C22—H22	119.9
C5—C6—C7	121.1 (3)	C22—C23—C24	119.8 (3)
C5—C6—H6	119.4	C22—C23—H23	120.1
C7—C6—H6	119.4	C24—C23—H23	120.1
N1—C7—C6	121.6 (3)	N3—C24—C23	122.0 (3)
N1—C7—C2	120.6 (2)	N3—C24—H24	119.0
C6—C7—C2	117.8 (3)	C23—C24—H24	119.0
C9—C8—C13	118.5 (3)	N3—C25—C21	123.6 (3)
C9—C8—N1	121.0 (3)	N3—C25—C26	116.4 (2)
C13—C8—N1	120.5 (2)	C21—C25—C26	120.1 (3)
C10—C9—C8	120.6 (3)	N2—C26—C18	123.8 (3)
C10—C9—H9	119.7	N2—C26—C25	115.8 (2)
C8—C9—H9	119.7	C18—C26—C25	120.3 (2)
O1—Cu1—N2—C15	142.7 (7)	C11—C12—C13—C14	−175.1 (3)
O4i—Cu1—N2—C15	−6.5 (3)	C9—C8—C13—C12	−0.3 (4)
N3—Cu1—N2—C15	179.8 (3)	N1—C8—C13—C12	−177.0 (3)
O3i—Cu1—N2—C15	−65.8 (3)	C9—C8—C13—C14	175.9 (3)
C14i—Cu1—N2—C15	−36.2 (3)	N1—C8—C13—C14	−0.8 (4)
O1—Cu1—N2—C26	−40.2 (8)	Cu1ii—O3—C14—O4	6.4 (2)
O4i—Cu1—N2—C26	170.57 (18)	Cu1ii—O3—C14—C13	−172.1 (3)
N3—Cu1—N2—C26	−3.10 (18)	Cu1ii—O4—C14—O3	−7.9 (3)
O3i—Cu1—N2—C26	111.35 (18)	Cu1ii—O4—C14—C13	170.6 (2)
C14i—Cu1—N2—C26	140.93 (18)	C12—C13—C14—O3	152.6 (3)
O1—Cu1—N3—C24	−1.7 (3)	C8—C13—C14—O3	−23.8 (4)
O4i—Cu1—N3—C24	130.9 (6)	C12—C13—C14—O4	−26.0 (4)
N2—Cu1—N3—C24	−177.4 (3)	C8—C13—C14—O4	157.7 (3)
O3i—Cu1—N3—C24	88.0 (3)	C12—C13—C14—Cu1ii	4.3 (10)
C14i—Cu1—N3—C24	89.9 (3)	C8—C13—C14—Cu1ii	−172.1 (7)
O1—Cu1—N3—C25	178.62 (19)	C26—N2—C15—C16	0.4 (4)
O4i—Cu1—N3—C25	−48.8 (7)	Cu1—N2—C15—C16	177.4 (2)
N2—Cu1—N3—C25	2.88 (18)	N2—C15—C16—C17	0.0 (5)
O3i—Cu1—N3—C25	−91.73 (19)	C15—C16—C17—C18	−0.4 (5)
C14i—Cu1—N3—C25	−89.8 (2)	C16—C17—C18—C26	0.3 (4)
O4i—Cu1—O1—C1	77.83 (18)	C16—C17—C18—C19	179.0 (3)
N3—Cu1—O1—C1	−108.10 (18)	C26—C18—C19—C20	0.6 (5)
N2—Cu1—O1—C1	−71.5 (8)	C17—C18—C19—C20	−178.1 (3)
O3i—Cu1—O1—C1	136.70 (18)	C18—C19—C20—C21	−1.3 (5)
C14i—Cu1—O1—C1	107.42 (18)	C19—C20—C21—C25	0.8 (5)
Cu1—O1—C1—O2	13.4 (3)	C19—C20—C21—C22	179.5 (3)
Cu1—O1—C1—C2	−167.57 (18)	C25—C21—C22—C23	0.2 (4)
O2—C1—C2—C3	160.8 (3)	C20—C21—C22—C23	−178.4 (3)
O1—C1—C2—C3	−18.2 (4)	C21—C22—C23—C24	−0.1 (5)
O2—C1—C2—C7	−19.0 (4)	C25—N3—C24—C23	0.7 (4)
O1—C1—C2—C7	162.0 (3)	Cu1—N3—C24—C23	−179.0 (2)
C7—C2—C3—C4	2.3 (4)	C22—C23—C24—N3	−0.4 (5)
C1—C2—C3—C4	−177.5 (3)	C24—N3—C25—C21	−0.5 (4)
C2—C3—C4—C5	1.8 (4)	Cu1—N3—C25—C21	179.2 (2)
C3—C4—C5—C6	−3.9 (5)	C24—N3—C25—C26	178.0 (3)
C4—C5—C6—C7	1.9 (5)	Cu1—N3—C25—C26	−2.2 (3)
C8—N1—C7—C6	29.3 (5)	C22—C21—C25—N3	0.1 (4)
C8—N1—C7—C2	−154.7 (3)	C20—C21—C25—N3	178.8 (3)
C5—C6—C7—N1	178.4 (3)	C22—C21—C25—C26	−178.4 (3)
C5—C6—C7—C2	2.3 (4)	C20—C21—C25—C26	0.3 (4)
C3—C2—C7—N1	179.6 (2)	C15—N2—C26—C18	−0.5 (4)
C1—C2—C7—N1	−0.6 (4)	Cu1—N2—C26—C18	−178.0 (2)
C3—C2—C7—C6	−4.2 (4)	C15—N2—C26—C25	−179.7 (3)
C1—C2—C7—C6	175.5 (2)	Cu1—N2—C26—C25	2.8 (3)
C7—N1—C8—C9	30.5 (5)	C17—C18—C26—N2	0.2 (4)
C7—N1—C8—C13	−152.8 (3)	C19—C18—C26—N2	−178.6 (3)
C13—C8—C9—C10	−1.3 (5)	C17—C18—C26—C25	179.3 (3)
N1—C8—C9—C10	175.4 (3)	C19—C18—C26—C25	0.6 (4)
C8—C9—C10—C11	2.0 (5)	N3—C25—C26—N2	−0.4 (4)
C9—C10—C11—C12	−1.0 (5)	C21—C25—C26—N2	178.2 (2)
C10—C11—C12—C13	−0.7 (5)	N3—C25—C26—C18	−179.6 (2)
C11—C12—C13—C8	1.3 (5)	C21—C25—C26—C18	−1.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	2.07	2.708 (5)	131
N1—H1···O3	0.86	2.06	2.701 (5)	130
C17—H17···O2iii	0.93	2.55	3.308 (4)	139
C23—H23···O3iv	0.93	2.38	3.185 (4)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.86	2.07	2.708 (5)	131
N1—H1⋯O3	0.86	2.06	2.701 (5)	130
C17—H17⋯O2i	0.93	2.55	3.308 (4)	139
C23—H23⋯O3ii	0.93	2.38	3.185 (4)	145

Symmetry codes: (i) ; (ii) .